In the late 1970s, Skyy signed to Salsoul Records. After several albums that saw moderate success in the R&B market, the group crossed over to the mainstream in a big way with the release of the Skyy Line album in late 1981. Featured on this album was the single "Call Me", which gave the group their first (and only, to date) top 40 hit on the pop charts, peaking at number 26 in 1982. It also became the first of several number one R&B hits for Skyy. Meanwhile, the group continued to record for the Salsoul label up through the release of their 1984 Inner City album (Salsoul would fold in 1985), scoring several additional hits on the R&B chart during that time.

In the mid-1980s, the group signed with Capitol Records and released their next album, From the Left Side in 1986. Apart from the top ten R&B single, "Givin' It (to You)", the album saw limited success, and the group left Capitol soon thereafter.

Things were looking rather bleak for the band by the late 1980s. However, after signing to Atlantic Records, Skyy launched a major comeback in 1989 with the release of their successful Start of a Romance album. This release spun off two number one R&B singles, with both the title track ("Start of a Romance") and the quiet storm classic, "Real Love" claiming the top spot. "Real Love" also became the group's second and final crossover pop hit peaking at number 47 on the Billboard Hot 100 chart in early 1990. The second single released from the album (between the title track and "Real Love"), "Love All the Way" also cracked the R&B top 50. By the release of the Nearer to You album in 1992, the hits had again dried up, and the band has not released a new studio album since then. Although Skyy is one of very few bands to release 12 studio albums in 12 years (two compilation albums), which turned out multiple hits, they often go unnoticed and unsung. In 2014, the French Nu-Disco act Solidisco released an updated version of Skyy's 1980 single "Here's To You", in which the group received credits due to the original version being used.